'Awards Chatter' Podcast — Mark Cuban ('Shark Tank')

The billionaire entrepreneur and philanthropist, who is an investor in more than 150 small businesses, an NBA team and an entertainment holding company, reflects on his experience as a reality TV host and the coronavirus crisis.
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Mark Cuban

Why, since 2011, has the billionaire businessman Mark Cuban agreed to appear on ABC's structured reality program Shark Tank, on which investors (or "sharks") decide whether or not to finance pitches from entrepreneurs? I posed the question when we sat down over the weekend — me in Los Angeles, him in Dallas — for the first remotely recorded episode of The Hollywood Reporter's Awards Chatter podcast. His answer? "Because it sends the message to everybody — particularly families and kids — that the American dream is alive and well. That's it. One hundred percent of it."

Today, with the novel coronavirus raging, Cuban is fighting to keep not just the American dream but businesses he's invested in alive and well. He has sizable financial interests in several of the areas that have been hardest hit by the pandemic: small businesses, some 150 of which he has backed through Shark Tank; professional sports, as the majority owner of the NBA’s Dallas Mavericks; and entertainment, as the co-owner, with Todd Wagner, of 2929 Entertainment, divisions of which include Magnolia Pictures and AXS TV. And last week, he agreed to advise President Donald Trump, his one-time reality show competitor and frequent sparring partner, on his Task Force to Reopen the Economy.

In other words, Cuban seemed an appropriate guest for our first episode since the outbreak and its devastating impact on the American economy.

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LISTEN: You can hear the entire interview below.

Past guests include Steven Spielberg, Oprah Winfrey, Lorne Michaels, Barbra Streisand, George Clooney, Meryl Streep, Robert De Niro, Jennifer Lawrence, Eddie Murphy, Gal Gadot, Warren Beatty, Angelina Jolie, Snoop Dogg, Jessica Chastain, Stephen Colbert, Reese Witherspoon, Aaron Sorkin, Margot Robbie, Ryan Reynolds, Nicole Kidman, Denzel Washington, Julia Louis-Dreyfus, Matthew McConaughey, Kate Winslet, Jimmy Kimmel, Natalie Portman, Chadwick Boseman, Jennifer Lopez, Elton John, Judi Dench, Quincy Jones, Jane Fonda, Tom Hanks, Amy Schumer, Justin Timberlake, Elisabeth Moss, RuPaul, Rachel Brosnahan, Jimmy Fallon, Kris Jenner, Michael Moore, Emilia Clarke, Lin-Manuel Miranda, Helen Mirren, Tyler Perry, Sally Field, Spike Lee, Lady Gaga, J.J. Abrams, Emma Stone, Al Pacino, Julia Roberts, Jerry Seinfeld, Dolly Parton, Will Smith, Taraji P. Henson, Sacha Baron Cohen, Carol Burnett and Norman Lear.

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Cuban was born into a blue-collar Pittsburgh family. His father was an upholsterer and his mother worked odd jobs, and while neither was college educated, both instilled in him the importance of working hard. His entrepreneurial spirit first manifested itself when he was just 12 years old and went door-to-door selling garbage bags in order to afford a pair of basketball sneakers that he coveted. A half-century later, he says, "That taught me more about sales than probably anything I've ever done."

He dropped out of high school, took some classes at the University of Pittsburgh and then enrolled at Indiana University's business school. To pay for his tuition, Cuban took on a variety of random jobs, like sending chain letters, promoting parties and running a bar — "My whole life was a side hustle," he says with a chuckle. He graduated in 1981, and, on July 4, 1982, he departed Bloomington in a beat-up 1977 Fiat X1/9 and drove to Dallas, where he moved into a three-bedroom apartment with five other friends.

In Dallas, Cuban landed a $1,500-a-month job at a computer software company, but not long thereafter he was unceremoniously fired — which he now describes as "the best thing that ever happened to me." He spent the next seven years raising funds and building his own computer consulting service, MicroSolutions, and then, at just 32, sold it to CompuServe for $6 million. After that? "I was retired," he says with a laugh, and he spent the next few years "partying like a rock star."

One day, while sitting in a California Pizza Kitchen with Todd Wagner, an Indiana classmate, Cuban came up with the project for which he would un-retire. "We were just swapping ideas," he recalls, "This was right when the internet was starting to happen — late '94 or early '95 — and I was like, 'Look, there has got to be a better way to listen to sports'" than over the radio. He and Wagner started a company — initially called AudioNet but later renamed Broadcast.com — that was one of the earliest streaming services. 

"We were YouTube before YouTube, we were Pandora, we were Spotify," Cuban says. "Anybody that does streaming right now was built on the back of what we did way back when." In July 1998, the company went public with the biggest IPO first-day burst in the history of the stock market — and Cuban was a billionaire. In 1999, Cuban and Wagner sold the company to Yahoo!, splitting $5.7 billion in Yahoo! stock. 

With his newfound massive wealth — which he jokingly calls "'fuck-you' money" — Cuban began venturing into areas about which he felt personally passionate, such as sports and entertainment. In 2000, the basketball lover bought his own team. And in the years thereafter, he ventured into Hollywood, assembling his own vertical operation — which at one time included the first high-def TV network (HDNet), film production companies (HDNet Movies for small films, 2929 Entertainment for big ones), a film distribution company (Magnolia) and a theater chain (Landmark) — through which he put out films that wound up with Oscar nominations, such as 2005's Enron: The Smartest Guys in the Room and Good Night, and Good Luck, and one of the first day-and-date releases, 2006's Bubble.

Cuban saw in reality TV an opportunity to pay it forward. His first stab at the genre was ABC's short-lived The Benefactor, which — to the delight of Trump, who was then hosting NBC's The Apprentice — lasted just six episodes. But in 2011, Cuban was lured back to the Alphabet Network, serving as a "guest shark" on the second season of Shark Tank. He has returned ever since as a regular, helping to turn the show into a massive hit and four-time Emmy winner, and investing in some 150 small businesses through the show.

For this shark, things were going rather, well, swimmingly — until March 11, when TV cameras caught his dumbfounded reaction as he sat courtside at a Mavericks game and learned that the rest of the NBA season was being suspended due to the coronavirus. ("I'm gonna be a meme for the rest of my life," he jokes.) The gravity of the crisis began to sink in, and Cuban responded to it early. He told ESPN that he would make sure all hourly workers at Dallas' American Airlines Center, where the Mavs play, would be paid for the duration of the shutdown. And when the Trump administration reached out to ask him to serve as an adviser, he set aside Trump's history of pettiness toward him and said yes.

Explains Cuban, "Donald's in it for himself, right? He'll definitely hold a grudge for a long time — until he needs you for something, and then the grudge is gone. He is who he is, and that's fine. And I actually don't dislike him — I mean, I like spending time with him, he's entertaining." Upon being asked about Trump's much-maligned response to the crisis, Cuban says, "I'm not gonna throw him under the bus and fuck with him for what he's done in the past. What matters now is what happens going forward."

Cuban, an Ayn Rand admirer with some Libertarian tendencies, flirted with the idea of challenging Trump as an independent candidate in the 2020 presidential election. "It's something I discussed with my family, and they voted it down," he says. "Otherwise I would have run." Now, as a presidential adviser rather than a candidate, he is touting what he calls "America 2.0" — what he hopes America will look like coming out of this crisis, from having a federal minimum wage to rewarding companies that offer their employees equity to "trickle-up economics."

Meanwhile, in an election season in which candidates such as Sen. Bernie Sanders and Sen. Elizabeth Warren have argued that billionaires shouldn't exist at all, Cuban has this to say: "People like me are going to get lucky, and we're going to rise to the top. Somebody has got to have the most amount of money. And — whether it's a billion or a million or whatever it may be — whoever is at the bottom isn't going to be happy with the people at the top. Period, end of story. But at the same time, we can be compassionate as capitalists."